Howland Blackiston was born and raised in New York City and has been invloved in drawing, painting and sculpting for many decades. After college, he studied at the National Academy, the Arts Students League, and the Parson's School of Design in New York.

His wife Joy (also raised in new York) was for years a professional theatrical costume designer, working at the Asolo Theatre, in Sarasota, Florida and the Roundabout Theatre in New York City.

Howland and his wife live in Weston, Connecticut and have a grown daughter, Brooke.